4-Fluoroaniline → 3-[4-p-Fluoroanilino-6-(1,1,3,3-tetramethylbutylamino)-s-triazin-2-yl]-3-azabicyclo[3.2.2]nonane

HRID 443764Notes

Reaction equation

HRID 443764 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]([CH3:16])([CH3:15])[CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])[N:5]=[C:4]([N:17]2[CH2:23][CH:22]3[CH2:24][CH2:25][CH:19]([CH2:20][CH2:21]3)[CH2:18]2)[N:3]=1.[F:26][C:27]1[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=1>CC(C)=O>[F:26][C:27]1[CH:33]=[CH:32][C:30]([NH:31][C:2]2[N:7]=[C:6]([NH:8][C:9]([CH3:15])([CH3:16])[CH2:10][C:11]([CH3:12])([CH3:14])[CH3:13])[N:5]=[C:4]([N:17]3[CH2:23][CH:22]4[CH2:24][CH2:25][CH:19]([CH2:20][CH2:21]4)[CH2:18]3)[N:3]=2)=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 155725803-[4-Chloro-6-(1,1,3,3-tetramethylbutylamino)-s-triazin-2-yl]-3-azabicyclo[3.2.2]nonane

Product 1

HCID 155725843-[4-p-Fluoroanilino-6-(1,1,3,3-tetramethylbutylamino)-s-triazin-2-yl]-3-azabicyclo[3.2.2]nonane

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Eight grams (0.022 mole) of 3-[4-chloro-6-(1,1,3,3-tetramethylbutylamino)-s-triazin-2-yl]-3-azabicyclo[3.2.2]nonane and 21 ml. (0.22 mole) of p-fluoroaniline is placed in a glass liner in a bomb and then heated in an oil bath maintained at 190°-205° C. for about 40 hours. After cooling, the indigo contents of the bomb are rinsed with chloroform and water into a flask and 50 ml. of 10 N NaOH is added. The solution is then evaporated in vacuo and the aqueous solution remaining is extracted with chloroform. The combined chloroform extracts are washed with water, dried over magnesium sulfate, filtered through Magnesol® and the Magnesol® washed with chloroform. Removal of solvent in vacuo, addition of toluene and re-evaporation in vacuo several times gives an orange solid which on slurrying with acetone gives white crystals. Recrystallization from acetone gives 7.1 g. of colorless crystals m.p. 173.5°-174.5° C.

Workup

  1. temperatureheated in an oil bath
  2. temperaturemaintained at 190°-205° C. for about 40 hours
  3. temperatureAfter cooling
  4. washthe indigo contents of the bomb are rinsed with chloroform and water into a flask
  5. additionof 10 N NaOH is added
  6. customThe solution is then evaporated in vacuo
  7. extractionthe aqueous solution remaining is extracted with chloroform
  8. washThe combined chloroform extracts are washed with water
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered through Magnesol®
  11. washthe Magnesol® washed with chloroform
  12. customRemoval of solvent
  13. additionin vacuo, addition of toluene and re-evaporation in vacuo several times
  14. customgives an orange solid which
  15. customgives white crystals
  16. customRecrystallization from acetone
  17. customgives 7.1 g

Sources & evidence

ORD record
ord-6d1593c1edc940eea046bce04841423b
Source dataset
uspto-grants-1981_04
Patent number
US04261892

Reaction notes

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